Asymmetric kinetic resolution of sulfides for the construction of unsymmetric sulfides and chiral 3,3-disubstituted oxindoles

被引：8
|
作者：
Wang, Kaiye [1 ]
Xiang, Yanan [1 ]
Shi, Zhujun [1 ]
Wang, Hongyu [1 ]
Li, Na [1 ]
Tang, Bo [1 ]
机构：
[1] Shandong Normal Univ, Inst Mol & Nano Sci, Collaborat Innovat Ctr Functionalized Probes Chem, Minist Educ,Key Lab Mol & Nano Probes,Coll Chem C, Jinan 250014, Shandong, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 26期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
ONE-POT SYNTHESIS; 1,6-CONJUGATE ADDITION; EFFICIENT SYNTHESIS; DISULFIDE; SULFENYLATION; OXIDATION; THIOLS;
D O I：
10.1039/c9ob01065c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A range of 3,3-disubstituted oxindoles accessed using para-quinone methides derived from isatins with thiols were used for the formation of unsymmetrical disulfides, and 3,3-disubstituted oxindoles with a chiral quaternary carbon center and unsymmetric disulfides could also be directly obtained with high selectivities catalyzed by chiral phosphines in one step.
引用
收藏
页码：6351 / 6354
页数：4
相关论文
共 50 条
  • [31] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles
    Cao, Zhong-Yan
    Zhou, Feng
    Zhou, Jian
    ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) : 1443 - 1454
  • [32] Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation
    Yasui, Yoshizumi
    Kamisaki, Haruhi
    Ishida, Takayuki
    Takemoto, Yoshiji
    TETRAHEDRON, 2010, 66 (11) : 1980 - 1989
  • [33] Synthesis of 3,3-Disubstituted Oxindoles by Palladium-Catalyzed Asymmetric Intramolecular -Arylation of Amides: Reaction Development and Mechanistic Studies
    Katayev, Dmitry
    Jia, Yi-Xia
    Sharma, Akhilesh K.
    Banerjee, Dipshikha
    Besnard, Celine
    Sunoj, Raghavan B.
    Kuendig, E. Peter
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (36) : 11916 - 11927
  • [34] Copper(I)-Catalyzed Asymmetric Hydrophosphination of 3,3-Disubstituted Cyclopropenes
    Zhang, Shuai
    Jiang, Nan
    Xiao, Jun-Zhao
    Lin, Guo-Qiang
    Yin, Liang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (40)
  • [35] Copper(I)-Catalyzed Asymmetric Hydrophosphination of 3,3-Disubstituted Cyclopropenes
    Zhang, Shuai
    Jiang, Nan
    Xiao, Jun-Zhao
    Lin, Guo-Qiang
    Yin, Liang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023,
  • [36] Rapid construction of γ-lactam containing 3,3-disubstituted oxindoles via a silver-catalyzed cascade radical bicyclization reaction
    Xie, Lin
    Cao, Ruizhe
    Huang, Yingxue
    Zhang, Qian
    Fang, Zeguo
    Li, Dong
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (21) : 5929 - 5934
  • [37] Transition-Metal-Mediated Routes to 3,3-Disubstituted Oxindoles through Anilide Cyclisation
    Klein, Johannes E. M. N.
    Taylor, Richard J. K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (34) : 6821 - 6841
  • [38] Rhodium-Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3-Disubstituted Oxindoles
    Jang, Young Jin
    Larin, Egor M.
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (39) : 11927 - 11930
  • [39] Chiral Acyl Radicals Generated by Visible Light Enable Stereoselective Access to 3,3-Disubstituted Oxindoles: Application toward the Synthesis of (-)- and (+)-Physovenine
    Spaeth, Josef
    Oddy, Meghan J.
    Hunter, Roger
    Petersen, Wade F. F.
    SYNTHESIS-STUTTGART, 2023, 55 (11): : 1736 - 1743
  • [40] Preparation of 3-Sulfonylated 3,3-Disubstituted Oxindoles by the Addition of Sulfinate Salts to 3-Halooxindoles
    Zuo, Jian
    Wu, Zhi-Jun
    Zhao, Jian-Qiang
    Zhou, Ming-Qiang
    Xu, Xiao-Ying
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 634 - 640
12345